Benzoxazolyl linked benzylidene based rhodanine and analogs as novel antidiabetic agents: synthesis, molecular docking, and in vitro studies

Benzoxazolyl linked meta- and para-substituted new chemical entities (5a–5h) featuring thiazolidinedione, rhodanine, hydantoin, and thiohydantoin moieties were synthesized and characterized by 1H NMR, 13C NMR, FT-IR, and HRMS spectral studies. In addition, all compounds were screened for α-glucosidase inhibitory activity and further supported by molecular docking studies carried out at the active site of α-glucosidase (PDB code: 3TOP) in comparison to acarbose used as a standard drug. Out of eight tested compounds, 5d was found as the most active inhibitor of α-glucosidase (IC50 = 9.48 ± 0.36 µM), having rhodanine moiety substituted at meta-position of the phenyl ring.